TOP 30 Vacation rentals on the bay in Maryland

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Pointe On The Bay is a charming lodging institution located at 2209 Philadelphia Avenue in Ocean City, Maryland, United States. Situated just steps away from the beautiful bay, this cozy retreat offers comfortable accommodations and stunning views. Guests can relax in spacious rooms, take a dip in the outdoor pool, or enjoy a leisurely stroll along the nearby boardwalk. With its convenient location and welcoming atmosphere, Pointe On The Bay is the perfect destination for a relaxing getaway by the water.

The Hyatt Regency Chesapeake Bay Golf Resort, Spa, and Marina is a luxurious lodging destination located in Cambridge, Maryland, United States. Situated on the picturesque U.S. 50, this institution offers a perfect blend of relaxation and recreation with its stunning waterfront views, championship golf course, rejuvenating spa treatments, and marina access. Guests can enjoy upscale accommodations, fine dining options, and a wide range of amenities to ensure a memorable stay. Whether you're looking to unwind in the spa, hit the links on the golf course, or explore the nearby attractions, the Hyatt Regency Chesapeake Bay Golf Resort, Spa, and Marina provides a truly unforgettable experience for all visitors.

M/V Bay Breeze is a charming bar and travel agency located at 208 Bank Street in the picturesque town of Chesapeake City, Maryland, United States. This unique establishment offers a relaxing and inviting atmosphere where patrons can enjoy a drink while planning their next adventure. With a focus on providing exceptional service and personalized travel experiences, M/V Bay Breeze is the perfect destination for those looking to unwind and explore new destinations. Whether you're stopping in for a cocktail or booking your next vacation, M/V Bay Breeze is sure to leave a lasting impression.

Back Bay Adventures is a travel agency located at 400 32nd Street in Ocean City, Maryland, United States. They offer a variety of exciting activities such as jet ski rentals, headboat bay fishing, private fishing charters, and private boat parties and cruises. Whether you are a family, a novice rider, or an experienced jet ski enthusiast, there is something for everyone at Back Bay Adventures. The Calico Jack, a Coast Guard inspected head boat, offers public bay fishing trips for up to 32 passengers. Private fishing charters are also available for those looking for a more personalized experience on the water. If you are celebrating a special occasion, consider booking a private boat party cruise with your friends and family.

Red Point Lighthouse Vacation Rentals is a unique real estate and travel agency located at 115 South Main Street, North East, Maryland, United States. Our lighthouse replica on the northern tip of the Chesapeake Bay offers stunning views and luxurious amenities. With 2 living rooms, an indoor hot tub, fully equipped kitchen, dining area for 12, and a propane grill, you'll have everything you need for a comfortable stay. Our property also features wheelchair access on the main floor, including a king bedroom, 4 bathrooms, a wet bar, fast WIFI, and smart TVs. Enjoy the wrap-around decks, 1.5 acres of land, and the community sandy beach just across the street. The master bedroom boasts a king bed, sea views, and a jacuzzi, while the main floor handicap accessible bedroom also has a king bed. Book your stay with us on Airbnb for a truly unforgettable experience.

Chesapeake Bay Rentals is a reputable real estate and travel agency located at 3010 Governor Run Road in Port Republic, Maryland. Specializing in vacation rentals along the stunning Chesapeake Bay, they offer a wide selection of properties to suit every traveler's needs. Whether you're looking for a cozy cottage for a romantic getaway or a spacious waterfront home for a family vacation, Chesapeake Bay Rentals has the perfect option for you. Their knowledgeable staff is dedicated to providing top-notch customer service and helping you find the ideal rental for your next trip to this beautiful region of the United States.

Wades Point Inn On The Bay is a charming waterfront lodging located at 10090 Wades Point Road in McDaniel, Maryland, United States. This peaceful retreat offers stunning views of the bay and a tranquil atmosphere perfect for relaxation and rejuvenation. The inn features comfortable accommodations, delicious breakfast options, and warm hospitality from the friendly staff. Guests can also enjoy activities such as kayaking, biking, and exploring the nearby towns. Whether you're looking for a romantic getaway or a peaceful escape, Wades Point Inn On The Bay is the perfect destination for your next vacation.

Chesapeake Bay Real Estate Plus is a versatile institution located at 108 North Talbot Street in Saint Michaels, Maryland. Serving as a general contractor, real estate agency, and travel agency, this one-stop shop offers a range of services to meet all your property and travel needs. Whether you're looking to buy or sell a home, plan a vacation, or renovate your property, Chesapeake Bay Real Estate Plus has you covered. With a team of experienced professionals and a commitment to customer satisfaction, this institution is your go-to destination for all things real estate and travel-related in the beautiful Chesapeake Bay area.

Located at 951 Fell Street in Baltimore, Maryland, Bay Dream Sailing is a premier tourist attraction and travel agency that offers unforgettable boat tours along the stunning waters of the Chesapeake Bay. Whether you're celebrating a special occasion like a birthday or anniversary, or simply looking for a unique way to explore the city, a boat tour with Bay Dream Sailing is a must-do activity in Baltimore. With private cruises available, you can enjoy a personalized and intimate experience on the water with your loved ones. Our experienced Captain, who is also the Commodore of the Sassafras River Yacht Club, has spent 25 years navigating the Chesapeake and is excited to share his passion for the waterways with you.

Chesapeake Bay Charter Services is a premier travel agency located at 910 Kentmorr Road in Stevensville, Maryland, United States. Specializing in charter services for exploring the beautiful Chesapeake Bay, they offer a wide range of customizable packages for fishing trips, sightseeing tours, and private cruises. With experienced captains and top-of-the-line equipment, Chesapeake Bay Charter Services guarantees a memorable and enjoyable experience on the water. Whether you're a seasoned angler or just looking to relax and take in the scenic views, this institution has everything you need for an unforgettable adventure on the Chesapeake Bay.

Murphy Point on the Chesapeake is a real estate and travel agency located at 9328 Atlantic Avenue in North Beach, Maryland, United States. If you own a vacation rental, you can list it with us and manage everything from inquiries to checkouts. With Houfy, you have the freedom to establish your brand and grow your business. Our platform has tens of thousands of reviews and verified listings, giving travelers the confidence to book your home. Murphy Point on the Chesapeake in North Beach is a vacation home that can accommodate up to 6 guests. It features 3 bedrooms, 1 bathroom, and was listed on Houfy in May 2019. Book your stay with us for a relaxing getaway on the beautiful Chesapeake Bay.

Blackwater Adventures Chesapeake Bay is a premier travel agency and store located in Cambridge, Maryland, United States. Situated at 2524 Key Wallace Drive, this institution offers a wide range of exciting and adventurous experiences for those looking to explore the beauty of the Chesapeake Bay region. From guided kayak tours to fishing excursions, Blackwater Adventures is dedicated to providing unforgettable outdoor experiences for all ages and skill levels. Whether you're a seasoned outdoor enthusiast or a first-time adventurer, Blackwater Adventures Chesapeake Bay is the perfect destination for those seeking a thrilling and immersive exploration of the stunning natural landscapes of the Chesapeake Bay.

Mallows Bay Boat Ramp is a picturesque park located at 1440 Wilson Landing Road in Nanjemoy, Maryland, United States. This scenic spot offers a boat ramp for easy access to the water, making it a popular destination for boating and fishing enthusiasts. The park also features picnic areas and walking trails, providing visitors with the perfect opportunity to enjoy the beautiful surroundings. Whether you're looking to spend a relaxing day on the water or explore the natural beauty of the area, Mallows Bay Boat Ramp is the perfect place to visit.

The Tilghman Island Inn is a charming waterfront retreat located on the picturesque Tilghman Island in Maryland, United States. This historic institution offers a unique blend of food, lodging, and restaurant services, making it the perfect destination for a relaxing getaway or a delicious dining experience. Situated at 21384 Coopertown Road, the Tilghman Island Inn boasts stunning views of the Chesapeake Bay and a warm, inviting atmosphere that will make you feel right at home. Whether you're looking to enjoy a gourmet meal at the on-site restaurant, unwind in one of the cozy guest rooms, or simply take in the natural beauty of the surrounding area, this institution has something for everyone.

Sundance Sailing Charters is a premier travel agency located at 78 George Street in Georgetown, Maryland, United States. Specializing in unforgettable sailing adventures, they offer a variety of charter options for exploring the beautiful waters of the Chesapeake Bay and beyond. Whether you're looking for a relaxing day on the water or a week-long sailing excursion, Sundance Sailing Charters has you covered. Their experienced crew and top-of-the-line vessels ensure a safe and enjoyable experience for all passengers. Book your next sailing adventure with Sundance Sailing Charters and create memories that will last a lifetime.

Miss Ocean City Fishing is the premier bay fishing boat in Ocean City, Maryland. Our 52-foot boat is certified by the United States Coast Guard and offers a clean and comfortable experience for all passengers. With plenty of seating and a clean restroom onboard, our 3-hour bay fishing trips are perfect for both experienced anglers and those new to fishing. We prioritize the comfort of our guests by limiting our trips to a maximum of 33 passengers, ensuring a more personalized experience. Book your trip online using special codes and secure your spot on the best bay fishing boat in Ocean City!

Ruby's Sea Glass Cottage is a charming real estate and travel agency located at 303 Ericsson Avenue in the picturesque town of Betterton, Maryland. Specializing in beachfront properties and vacation rentals, this institution offers a unique and personalized experience for those looking to explore the beauty of the Chesapeake Bay area. With a focus on relaxation and luxury, Ruby's Sea Glass Cottage is the perfect destination for those seeking a peaceful retreat by the sea. Let us help you find your perfect seaside oasis today.

White Crystal Beach is a charming lodging institution located on White Crystal Beach Road in the picturesque town of Earleville, Maryland. Situated right on the waterfront of the Chesapeake Bay, this tranquil retreat offers guests a peaceful and serene setting to relax and unwind. The cozy accommodations provide stunning views of the crystal-clear waters and sandy beaches, making it the perfect destination for a beach getaway. Whether you're looking to enjoy water activities, explore the nearby nature trails, or simply bask in the sun on the beach, White Crystal Beach is the ideal place to escape the hustle and bustle of everyday life. Experience the beauty of the Chesapeake Bay at White Crystal Beach.

Terri Kulp - Coldwell Banker Chesapeake Real Estate is a premier real estate institution located at 114B South Cross Street in Chestertown, Maryland. Specializing in waterfront properties, vacation homes, military relocations, and first-time homebuyers, Terri Kulp offers personalized assistance to help you find your dream home in this charming region along the Chesapeake Bay. With offices strategically located in Easton, Chestertown, and Chesapeake City, Coldwell Banker Chesapeake Real Estate provides unparalleled services to guide you through the process of buying or selling a home in the Eastern Shore of Maryland, Delaware, and Chester County, PA. Whether you are looking to upsize, downsize, or find your waterfront luxury dream home, Terri Kulp and her team are dedicated to helping you make informed decisions on your real estate journey. Contact Coldwell Banker Chesapeake Real Estate today to begin your search for the perfect home in this picturesque part of the country.

Mad Men Lake House is a unique lodging institution located at 2237 Marsh Hill Road in McHenry, Maryland, United States. Our properties have a mid-century modern feel with signature features such as swing chairs, record players with Bluetooth capability, outdoor string lights, and custom painted geometric wall designs. One of our properties is a 3 bedroom, 2 full bath bay front home that sleeps 8 and is just a 5-8 minute walk to the beach. We provide two kayaks and the community offers pools, tennis courts, shuffleboard, and mini-golf in the summer.

Harris Cove Cottages Bed 'N Boat is a charming lodging establishment located at 8080 Bozman Neavitt Road in the picturesque town of Saint Michaels, Maryland, United States. Situated right by the water, guests can enjoy stunning views of the cove and easy access to various water activities. The cozy cottages offer a comfortable and relaxing stay, perfect for a weekend getaway or a longer vacation. With boat rentals available on site, guests can explore the surrounding waters and experience the beauty of the Chesapeake Bay. Come stay at Harris Cove Cottages Bed 'N Boat for a peaceful retreat by the water.

Rodo Beach Cottage is a charming lodging option located at 15053 Chesapeake Bay Drive in Scotland, Maryland, United States. This cozy cottage is not only a place to stay, but also a real estate and travel agency. Whether you're looking for a relaxing getaway by the beach or interested in purchasing your own piece of paradise, Rodo Beach Cottage can help make your dreams a reality. With its beautiful location and personalized service, Rodo Beach Cottage is the perfect choice for your next vacation or real estate investment.

Watermark Tours, Charters, Cruises is a premier tourist attraction and travel agency located at 1 Dock Street in the charming city of Annapolis, Maryland, United States. Offering a variety of tours, private charters, and scenic cruises, visitors can explore the historic waterfront and iconic sites of Annapolis from the water. With knowledgeable guides, luxurious vessels, and unforgettable experiences, Watermark Tours, Charters, Cruises is the perfect destination for those seeking to discover the beauty and history of this picturesque city. Whether you're looking for a relaxing cruise, a private charter for a special occasion, or a guided tour of Annapolis, this institution has something for every traveler.

The Inn at Huntingfield Creek is a charming bed and breakfast located in Rock Hall, Maryland. Situated on 70 acres of peaceful land, our inn offers a variety of accommodations including guest rooms in the Manor House and private cottages. Guests can enjoy breathtaking sunsets, colorful gardens, and a romantic pond during their stay. With a focus on casual elegance, our inn provides a welcoming and relaxed atmosphere for guests to unwind and reconnect. Whether you're looking for a romantic getaway, a wedding venue, or a special event location, the Inn at Huntingfield Creek has everything you need.

The Inn at Perry Cabin is a luxurious lodging institution located at 308 Watkins Lane in Saint Michaels, Maryland, United States. Situated just across the Chesapeake Bay, this premier resort offers a tranquil escape from the hustle and bustle of everyday life. Surrounded by the beauty of the Eastern Shore, guests can enjoy the peaceful sounds of leaves rustling in the wind and the gentle flow of the water. At the Spa at Perry Cabin, guests can indulge in a variety of wellness programs inspired by the natural beauty of the region. From Peloton sessions to yoga on the banks of the Miles River, there are plenty of opportunities to nourish both body and soul. The Inn also offers unique spaces for intimate ceremonies and grand celebrations, making it a perfect setting for weddings and honeymoons.

The Inn at Haven Harbour is a charming waterfront lodging located at 20950 Rock Hall Avenue in Rock Hall, Maryland, United States. Nestled along the picturesque shores of the Chesapeake Bay, this cozy inn offers a tranquil retreat for guests seeking relaxation and comfort. With well-appointed rooms, breathtaking views, and top-notch amenities, the Inn at Haven Harbour is the perfect destination for a romantic getaway, family vacation, or weekend escape. Whether you're looking to explore the local attractions, enjoy water activities, or simply unwind by the water's edge, this hidden gem provides a welcoming atmosphere and personalized service to ensure a memorable stay. Experience the beauty of the Eastern Shore at the Inn at Haven Harbour.

Osprey Point Inn is a charming waterfront retreat located on Rock Hall Avenue in the picturesque town of Rock Hall, Maryland. This institution offers a unique blend of food, lodging, and dining options, making it the perfect destination for those looking to relax and unwind by the water. The inn features cozy and comfortable accommodations, delicious on-site dining options, and stunning views of the Chesapeake Bay. Guests can enjoy a peaceful and serene atmosphere, perfect for a romantic getaway or a relaxing weekend escape. Whether you're looking to enjoy a delicious meal at the restaurant, unwind in a cozy room, or simply take in the beautiful surroundings, Osprey Point Inn has something for everyone.

Sandaway Suites & Beach is a luxurious waterfront property located on the picturesque West Strand Road in Oxford, Maryland. Our institution offers a unique combination of health and wellness services, upscale lodging accommodations, real estate agency services, and personalized travel planning assistance. Guests can enjoy stunning views of the Chesapeake Bay from their spacious suites, relax on the private sandy beach, and take advantage of our on-site amenities such as a fitness center and spa. Whether you are looking for a rejuvenating retreat, a dream vacation home, or assistance with planning your next adventure, Sandaway Suites & Beach is the perfect destination for those seeking a truly unforgettable experience.

St. Michaels Harbour Inn, Marina & Spa is a luxurious year-round lodging option situated on the historic harbor of St. Michaels, Maryland. Easily accessible by both land and water, this institution is a convenient choice for travelers coming from major cities like Washington, D.C., Baltimore, Philadelphia, Richmond, and New York. The charming town of St. Michaels, known as the "heart and soul of the Chesapeake Bay," provides the perfect backdrop for a spontaneous overnight stay or a relaxing vacation. With its rich maritime history, picturesque waterways for kayaking, boutique shopping, antique hunting, and delicious seafood dining options, there is something for everyone to enjoy in this vintage port town.

Hilton Garden Inn Kent Island is a charming lodging institution located at 3206 Main Street in Grasonville, Maryland, United States. Situated on the picturesque Kent Island, this hotel offers comfortable accommodations and modern amenities for both leisure and business travelers. Guests can enjoy spacious rooms, on-site dining options, a fitness center, and a beautiful outdoor pool. The hotel's convenient location provides easy access to nearby attractions such as the Chesapeake Bay Bridge and historic downtown Annapolis. Whether you are visiting for a relaxing getaway or a productive business trip, Hilton Garden Inn Kent Island is the perfect choice for your stay.